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Synthesis of CLA-rich lysophosphatidylcholine by immobilized MAS1-H108A-catalyzed esterification: effects of the parameters and monitoring of the reaction process

Conjugated linoleic acid (CLA)‐rich lysophosphatidylcholine (LPC) with many proven beneficial effects is successfully synthesized by an immobilized mutant lipase (MAS1‐H108A)‐catalyzed esterification of glycerophosphorylcholine (GPC) and CLA‐rich FAs. Under the optimized conditions (temperature of 5...

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Main Authors: Li, Daoming, Wang, Weifei, Zhang, Li, Liu, Nan, Faiza, Muniba, Tan, Chin Ping, Yang, Bo, Lan, Dongming, Wang, Yonghua
Format: Article
Language:English
Published: Wiley 2018
Online Access:http://psasir.upm.edu.my/id/eprint/74062/1/Synthesis%20of%20CLA-rich%20lysophosphatidylcholine%20by%20immobilized%20MAS1-H108A-catalyzed%20esterification%20effects%20of%20the%20parameters%20and%20monitoring%20of%20the%20reaction%20process.pdf
http://psasir.upm.edu.my/id/eprint/74062/
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spelling my.upm.eprints.740622020-04-26T21:45:28Z http://psasir.upm.edu.my/id/eprint/74062/ Synthesis of CLA-rich lysophosphatidylcholine by immobilized MAS1-H108A-catalyzed esterification: effects of the parameters and monitoring of the reaction process Li, Daoming Wang, Weifei Zhang, Li Liu, Nan Faiza, Muniba Tan, Chin Ping Yang, Bo Lan, Dongming Wang, Yonghua Conjugated linoleic acid (CLA)‐rich lysophosphatidylcholine (LPC) with many proven beneficial effects is successfully synthesized by an immobilized mutant lipase (MAS1‐H108A)‐catalyzed esterification of glycerophosphorylcholine (GPC) and CLA‐rich FAs. Under the optimized conditions (temperature of 55 °C, substrate molar ratio of CLA‐rich FAs to GPC of 40:1, and enzyme loading of 300 U g−1), LPC content as high as 89.10 mol.% is achieved, which is exceptionally higher than any ever‐reported value. By monitoring the esterification process, it is found that sn1‐LPC is easy to synthesize and is the predominant product, while sn2‐LPC and phosphatidylcholine (PC) are difficult to synthesize and are with lower content in the final product. The formed sn2‐LPC during esterification may mainly attribute to the acyl migration of sn1‐LPC and the ratio of sn1‐LPC to sn2‐LPC finally plateaus at approximately 7. Besides, our results also demonstrate that sn2‐LPC is the main template for the synthesis of PC. Finally, a complete reaction scheme for the synthesis of LPC by immobilized MAS1‐H108A‐catalyzed esterification of GPC and fatty acids is mapped out. Overall, the highest LPC content can be obtained by immobilized MAS1‐H108A‐catalyzed esterification and there is the first study for systematical studying the reaction process of CLA‐rich LPC synthesis. Wiley 2018 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/74062/1/Synthesis%20of%20CLA-rich%20lysophosphatidylcholine%20by%20immobilized%20MAS1-H108A-catalyzed%20esterification%20effects%20of%20the%20parameters%20and%20monitoring%20of%20the%20reaction%20process.pdf Li, Daoming and Wang, Weifei and Zhang, Li and Liu, Nan and Faiza, Muniba and Tan, Chin Ping and Yang, Bo and Lan, Dongming and Wang, Yonghua (2018) Synthesis of CLA-rich lysophosphatidylcholine by immobilized MAS1-H108A-catalyzed esterification: effects of the parameters and monitoring of the reaction process. European Journal of Lipid Science and Technology, 120 (6). art. no. 1700529. pp. 1-7. ISSN 1438-7697; ESSN: 1438-9312 10.1002/ejlt.201700529
institution Universiti Putra Malaysia
building UPM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Putra Malaysia
content_source UPM Institutional Repository
url_provider http://psasir.upm.edu.my/
language English
description Conjugated linoleic acid (CLA)‐rich lysophosphatidylcholine (LPC) with many proven beneficial effects is successfully synthesized by an immobilized mutant lipase (MAS1‐H108A)‐catalyzed esterification of glycerophosphorylcholine (GPC) and CLA‐rich FAs. Under the optimized conditions (temperature of 55 °C, substrate molar ratio of CLA‐rich FAs to GPC of 40:1, and enzyme loading of 300 U g−1), LPC content as high as 89.10 mol.% is achieved, which is exceptionally higher than any ever‐reported value. By monitoring the esterification process, it is found that sn1‐LPC is easy to synthesize and is the predominant product, while sn2‐LPC and phosphatidylcholine (PC) are difficult to synthesize and are with lower content in the final product. The formed sn2‐LPC during esterification may mainly attribute to the acyl migration of sn1‐LPC and the ratio of sn1‐LPC to sn2‐LPC finally plateaus at approximately 7. Besides, our results also demonstrate that sn2‐LPC is the main template for the synthesis of PC. Finally, a complete reaction scheme for the synthesis of LPC by immobilized MAS1‐H108A‐catalyzed esterification of GPC and fatty acids is mapped out. Overall, the highest LPC content can be obtained by immobilized MAS1‐H108A‐catalyzed esterification and there is the first study for systematical studying the reaction process of CLA‐rich LPC synthesis.
format Article
author Li, Daoming
Wang, Weifei
Zhang, Li
Liu, Nan
Faiza, Muniba
Tan, Chin Ping
Yang, Bo
Lan, Dongming
Wang, Yonghua
spellingShingle Li, Daoming
Wang, Weifei
Zhang, Li
Liu, Nan
Faiza, Muniba
Tan, Chin Ping
Yang, Bo
Lan, Dongming
Wang, Yonghua
Synthesis of CLA-rich lysophosphatidylcholine by immobilized MAS1-H108A-catalyzed esterification: effects of the parameters and monitoring of the reaction process
author_facet Li, Daoming
Wang, Weifei
Zhang, Li
Liu, Nan
Faiza, Muniba
Tan, Chin Ping
Yang, Bo
Lan, Dongming
Wang, Yonghua
author_sort Li, Daoming
title Synthesis of CLA-rich lysophosphatidylcholine by immobilized MAS1-H108A-catalyzed esterification: effects of the parameters and monitoring of the reaction process
title_short Synthesis of CLA-rich lysophosphatidylcholine by immobilized MAS1-H108A-catalyzed esterification: effects of the parameters and monitoring of the reaction process
title_full Synthesis of CLA-rich lysophosphatidylcholine by immobilized MAS1-H108A-catalyzed esterification: effects of the parameters and monitoring of the reaction process
title_fullStr Synthesis of CLA-rich lysophosphatidylcholine by immobilized MAS1-H108A-catalyzed esterification: effects of the parameters and monitoring of the reaction process
title_full_unstemmed Synthesis of CLA-rich lysophosphatidylcholine by immobilized MAS1-H108A-catalyzed esterification: effects of the parameters and monitoring of the reaction process
title_sort synthesis of cla-rich lysophosphatidylcholine by immobilized mas1-h108a-catalyzed esterification: effects of the parameters and monitoring of the reaction process
publisher Wiley
publishDate 2018
url http://psasir.upm.edu.my/id/eprint/74062/1/Synthesis%20of%20CLA-rich%20lysophosphatidylcholine%20by%20immobilized%20MAS1-H108A-catalyzed%20esterification%20effects%20of%20the%20parameters%20and%20monitoring%20of%20the%20reaction%20process.pdf
http://psasir.upm.edu.my/id/eprint/74062/
_version_ 1665896006102810624
score 13.211869

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